Reduction of organic compounds.



' example, as fatty acids and their esters.

' which the'mixture may be. stirred. I The contained air is preferablyexhausted ered from the reaction product and the forrepresented thus:

uurra snares rauiar sures.

ERIC BERKELEY HIGGINS, 0F WALLASEY,- ENGLANI).

REDUCTION or ORGANIC ooMroUNns.

No Drawing.

To all whom it may concern:

Be it known that I, ERIC BERKELEY HIG- en's, Ph. D., asub'ject of theKing of Great. :Britain and Ireland, residing at WVallascy, Cheshire,England, have invented certain new anduseful Improvements in andRelating 'to the Reduction of Organic Compounds, of which the'followingis a specification. I

This invention relates to a process for the reduction of organiccompounds such, for

Processes'are known in which fatty acids and other bodies are saturatedin the presence of 'gaseous hydrogen and a catalyst,

. and the present invention hasfor its object to render unnecessary theuse of gaseous hydrogen "for the purpose, and to effect reduction by theuse of a re-agent which itself contains the hydrogen necessary andwhichat the same time may serve as the catalyst. j

According to "theinvention I effect the reduction of such compounds inthe presence of a me tallic formate, without employing gaseous hvdrogen.

In carrying the invention into effect in its application to unsaturatedfatty acids or their esters, these ,bodies "are intimately mixed withthe salt of formicacid and a catalytic substance (or a body capable offorming a catalytic substance by the action of the formate under theconditions ofthe treatment)- or a catalytic formate at the ordinarytemperature, and the mixture is then placed in a vessel capable of beingren dere'd gastight and preferably provide; with an agitating apparatusby means o from the vessel or displaced by a non-oxidiz ng gas-such ascarbon IIlQIlOXlCl, n1trogen, carbon dioxidor hydrogen and thetemperature then carefully raised when the reaction takes place whichwith a m0n'ovalent salt of formic acid may, for example, be

CH3 :5. CH2)x CH=CH arm COOH+2ROOCH= CH3... .(GHz); 4 CBzCHz (CH2)COOH-i-RgCOrl-CO;

The end products vary'with the formate".-

used, that is, with some formates, the re;

'sultingmetallic carbonate is unstable-and ester is brought about inessentially the carbon dioxid is evolved as well as carbon monoxld. Inany case, however, thesaturatlon of the unsaturated fatty acid or itssame manner. Owing to the evolution of Specification of Letters Patent.Application filed May 15, 1913. Serial 370. 767,814.

the pressure existing in the time of so heating.

,I atented-Feb. s, rare.

carbon dioxid' or carbon monoxid or both,

considerable pressures. are generated. i

The following. are various practical examples of the mannenin which theinven-' tion may be carried .into effect: 1. Nickel formate may be usedas the reducing'agent and thecatalyst. 2. Zinc formatemay be used as thereducing agent together with a known'cataly'st. 3. Zinc formate may beused as the reducing agent and -may-- be mixed, for example, Withpalladium chlorid Tho heating must be conducted with care,

which under the conditions of working is as local superheating is liableto cause spontaneous formation of oxalate from the formate and is liableto produce explosion. For this reason the apparatus must be providedwith necessary safetydevices.

' The reaction can be conducted practically quantitatively, but forcommercial purposes an excess of the reagent over the theoretical amountnecessary is preferably employed. The bodies taking part in theaction-should be dry.

,As regards"temperature, this may vary.

with the formate-ormix'ture of formates or other reagents 'employed butin general may be in theneighborhood of 20, below the point at. whichtheformate used spon taneously decomposes to the oxalate under theapparatus at The velocity of the reaction depends ortion and characterof the catalyzer used. In 'm:ost cases the base" from which the formateis originally prepared can be recov- (other 3 things being equal) uponthe pro-I mate be. re-synthesized therefrom for reuse in'the knownmanner for which purpose of re-synthesisthe carbon monoXid evolved bythe reduction may serve wholly or in "saturated organic compounds] bycatalysis, .consl'stingfrin treating the saidcompounds bya'dmixture witha formate and with a catalyst, and by heating the mixture, sub-:StaI'lt/lally as described.

2. A process for the hydrogenation of unsaturated organic compounds bycatalysis,

consisting in treating the said; compounds by admixture with a formateand with a catalyst, and by heating the mixture in a vessel from whichair .has been exhausted,

substantially as described.

3. A process for the hydrogenation of unsaturated organic compounds bycatalysis,

consisting in treating the said compounds by admixture with a formateand with a catalyst and by heating the mixture in a vessel'in thepresence of a non-oxidizing gas that has no chemical action on thecatalyst or body: to be reduced; substantially as described.

4;. A process for the hydrogenation of unsaturated fatty compoundscontaining as the essential constituent an unsaturated fatty acidradical, consisting; in treating the said compounds by admixture with aformate and with a catalyst, and by heating the mixture, substantiallyas described.

A process for the hydrogenation of unsaturated'fatty compoundscontaining as the essential constituent an unsaturated fatty acidradical, by catalysis, consisting in treating the said compounds byadmixture with a formate and with a catalyst, and byheating the mixturein a vessel from which air has been exhausted, substantially asdescribed.

.6. A process for the hydrogenation of unsaturated fatty compoundscontaining as the essential constituent an unsaturated fatty acidradical, consisting in treating the said compounds by admixture with aformate and with a catalyst, and by heating the mixture, substantiallyas described.

7. A process for the hydrogenation of unsaturated organic compounds bycatalysis, consisting in-treating the said compounds by admixture with aformate and with a body which under the conditions of Working isconverted into a catalytic substance by the action of the formate usedand then heating the mixture, substantially as described.

8. A process for the hydrogenation of unsaturatedorganic compounds bycatalysis, consisting in treating the said compounds by admixture with aformate and with a body which under the conditions of working isconverted into a catalytic substance by the action of'the formate used,and heating the mixture in a vessel from which air has been exhausted,substantially as described.

9. A process for the hydrogenation of unsaturated fattycompoundscontaining as the essential constituent an unsaturated fatty acidradical, by catalysis, consisting in treating the said compounds byadmixture with a formate and with a body which under the conditions ofworking is converted into a

